Barnstable County, Massachusetts Land For Sale (93 results)

At the western end of Osterville's legendary Sea View Avenue--a road many believe is one of the most beautiful and valuable on all of Cape Cod reveals a property that transcends the idea of a residence. On over one acre of sweeping, tree-lined greensward with glimpses of West Bay shimmering in the distance, here is a residence that is not simply lived in, but experienced. Accessed by a winding drive of hand-laid paver stones with more than 6,342 square feet of living space, this Merle Thorpe designed home is a masterpiece of craftsmanship from a bygone era. Every lovingly maintained detail speaks to a time when artistry, skill, and pride shaped construction: mahogany windows and doors, wide-plank quarter-sawn oak floors, artisan cabinetry and moldings and graceful curved walls and rooflines that play against the endless blue of Cape Cod skies. It is at once a home and a work of art--a sculpture you inhabit, revealing new secrets and surprises with every visit. The accommodations are generous: seven bedrooms in the main house, and a generously oversized bespoke 1,000+- square foot one-bedroom guest suite with full bath, Pullman refreshment bar and laundry room above the three-car garage complete with radiant heated floors. Even the practical details carry refinement, from a dedicated trash room with an automatic air-venting system to carefully considered storage and systems. The partially finished terrace level offers a bedroom, full bath, laundry room, an additional washing room and space for your imagination to run wild. Outside, the grounds invite leisure and celebration. A 50-foot gunite pool with auto-cover is framed by a stone terrace shaded by Japanese maplesan idyllic setting for alfresco dining on summer evenings, where the sound of waves rolling onto the shore drifts from across the avenue. Ownership here includes something rare: deeded rights to a private pristine Nantucket Sound beach, just steps away, and access to Eel River, perfect for launching kayaks and paddleboards. Welcome to 850 Sea View Avenue, more than a residence; it is a legacy. Built with unmatched skill and devotion, it offers its next steward more than shelter. It is a place where cherished memories are ingrained against a backdrop of beauty and heritage and where every wall, every curve and every view reveal a story of timeless artistry. Please verify all information contained herein.

At the western end of Osterville's legendary Sea View Avenue--a road many believe is one of the most beautiful and valuable on all of Cape Cod reveals a property that transcends the idea of a residence. On over one acre of sweeping, tree-lined greensward with glimpses of West Bay shimmering in the distance, here is a residence that is not simply lived in, but experienced. Accessed by a winding drive of hand-laid paver stones with more than 6,342 square feet of living space, this Merle Thorpe designed home is a masterpiece of craftsmanship from a bygone era. Every lovingly maintained detail speaks to a time when artistry, skill, and pride shaped construction: mahogany windows and doors, wide-plank quarter-sawn oak floors, artisan cabinetry and moldings and graceful curved walls and rooflines that play against the endless blue of Cape Cod skies. It is at once a home and a work of art--a sculpture you inhabit, revealing new secrets and surprises with every visit. The accommodations are generous: seven bedrooms in the main house, and a generously oversized bespoke 1,000+- square foot one-bedroom guest suite with full bath, Pullman refreshment bar and laundry room above the three-car garage complete with radiant heated floors. Even the practical details carry refinement, from a dedicated trash room with an automatic air-venting system to carefully considered storage and systems. The partially finished terrace level offers a bedroom, full bath, laundry room, an additional washing room and space for your imagination to run wild. Outside, the grounds invite leisure and celebration. A 50-foot gunite pool with auto-cover is framed by a stone terrace shaded by Japanese maplesan idyllic setting for alfresco dining on summer evenings, where the sound of waves rolling onto the shore drifts from across the avenue. Ownership here includes something rare: deeded rights to a private pristine Nantucket Sound beach, just steps away, and access to Eel River, perfect for launching kayaks and paddleboards. Welcome to 850 Sea View Avenue, more than a residence; it is a legacy. Built with unmatched skill and devotion, it offers its next steward more than shelter. It is a place where cherished memories are ingrained against a backdrop of beauty and heritage and where every wall, every curve and every view reveal a story of timeless artistry. Please verify all information contained herein.

At the western end of Osterville's legendary Sea View Avenue--a road many believe is one of the most beautiful and valuable on all of Cape Cod reveals a property that transcends the idea of a residence. On over one acre of sweeping, tree-lined greensward with glimpses of West Bay shimmering in the distance, here is a residence that is not simply lived in, but experienced. Accessed by a winding drive of hand-laid paver stones with more than 6,342 square feet of living space, this Merle Thorpe designed home is a masterpiece of craftsmanship from a bygone era. Every lovingly maintained detail speaks to a time when artistry, skill, and pride shaped construction: mahogany windows and doors, wide-plank quarter-sawn oak floors, artisan cabinetry and moldings and graceful curved walls and rooflines that play against the endless blue of Cape Cod skies. It is at once a home and a work of art--a sculpture you inhabit, revealing new secrets and surprises with every visit. The accommodations are generous: seven bedrooms in the main house, and a generously oversized bespoke 1,000+- square foot one-bedroom guest suite with full bath, Pullman refreshment bar and laundry room above the three-car garage complete with radiant heated floors. Even the practical details carry refinement, from a dedicated trash room with an automatic air-venting system to carefully considered storage and systems. The partially finished terrace level offers a bedroom, full bath, laundry room, an additional washing room and space for your imagination to run wild. Outside, the grounds invite leisure and celebration. A 50-foot gunite pool with auto-cover is framed by a stone terrace shaded by Japanese maplesan idyllic setting for alfresco dining on summer evenings, where the sound of waves rolling onto the shore drifts from across the avenue. Ownership here includes something rare: deeded rights to a private pristine Nantucket Sound beach, just steps away, and access to Eel River, perfect for launching kayaks and paddleboards. Welcome to 850 Sea View Avenue, more than a residence; it is a legacy. Built with unmatched skill and devotion, it offers its next steward more than shelter. It is a place where cherished memories are ingrained against a backdrop of beauty and heritage and where every wall, every curve and every view reveal a story of timeless artistry. Please verify all information contained herein.

At the western end of Osterville's legendary Sea View Avenue--a road many believe is one of the most beautiful and valuable on all of Cape Cod reveals a property that transcends the idea of a residence. On over one acre of sweeping, tree-lined greensward with glimpses of West Bay shimmering in the distance, here is a residence that is not simply lived in, but experienced. Accessed by a winding drive of hand-laid paver stones with more than 6,342 square feet of living space, this Merle Thorpe designed home is a masterpiece of craftsmanship from a bygone era. Every lovingly maintained detail speaks to a time when artistry, skill, and pride shaped construction: mahogany windows and doors, wide-plank quarter-sawn oak floors, artisan cabinetry and moldings and graceful curved walls and rooflines that play against the endless blue of Cape Cod skies. It is at once a home and a work of art--a sculpture you inhabit, revealing new secrets and surprises with every visit. The accommodations are generous: seven bedrooms in the main house, and a generously oversized bespoke 1,000+- square foot one-bedroom guest suite with full bath, Pullman refreshment bar and laundry room above the three-car garage complete with radiant heated floors. Even the practical details carry refinement, from a dedicated trash room with an automatic air-venting system to carefully considered storage and systems. The partially finished terrace level offers a bedroom, full bath, laundry room, an additional washing room and space for your imagination to run wild. Outside, the grounds invite leisure and celebration. A 50-foot gunite pool with auto-cover is framed by a stone terrace shaded by Japanese maplesan idyllic setting for alfresco dining on summer evenings, where the sound of waves rolling onto the shore drifts from across the avenue. Ownership here includes something rare: deeded rights to a private pristine Nantucket Sound beach, just steps away, and access to Eel River, perfect for launching kayaks and paddleboards. Welcome to 850 Sea View Avenue, more than a residence; it is a legacy. Built with unmatched skill and devotion, it offers its next steward more than shelter. It is a place where cherished memories are ingrained against a backdrop of beauty and heritage and where every wall, every curve and every view reveal a story of timeless artistry. Please verify all information contained herein.

At the western end of Osterville's legendary Sea View Avenue--a road many believe is one of the most beautiful and valuable on all of Cape Cod reveals a property that transcends the idea of a residence. On over one acre of sweeping, tree-lined greensward with glimpses of West Bay shimmering in the distance, here is a residence that is not simply lived in, but experienced. Accessed by a winding drive of hand-laid paver stones with more than 6,342 square feet of living space, this Merle Thorpe designed home is a masterpiece of craftsmanship from a bygone era. Every lovingly maintained detail speaks to a time when artistry, skill, and pride shaped construction: mahogany windows and doors, wide-plank quarter-sawn oak floors, artisan cabinetry and moldings and graceful curved walls and rooflines that play against the endless blue of Cape Cod skies. It is at once a home and a work of art--a sculpture you inhabit, revealing new secrets and surprises with every visit. The accommodations are generous: seven bedrooms in the main house, and a generously oversized bespoke 1,000+- square foot one-bedroom guest suite with full bath, Pullman refreshment bar and laundry room above the three-car garage complete with radiant heated floors. Even the practical details carry refinement, from a dedicated trash room with an automatic air-venting system to carefully considered storage and systems. The partially finished terrace level offers a bedroom, full bath, laundry room, an additional washing room and space for your imagination to run wild. Outside, the grounds invite leisure and celebration. A 50-foot gunite pool with auto-cover is framed by a stone terrace shaded by Japanese maplesan idyllic setting for alfresco dining on summer evenings, where the sound of waves rolling onto the shore drifts from across the avenue. Ownership here includes something rare: deeded rights to a private pristine Nantucket Sound beach, just steps away, and access to Eel River, perfect for launching kayaks and paddleboards. Welcome to 850 Sea View Avenue, more than a residence; it is a legacy. Built with unmatched skill and devotion, it offers its next steward more than shelter. It is a place where cherished memories are ingrained against a backdrop of beauty and heritage and where every wall, every curve and every view reveal a story of timeless artistry. Please verify all information contained herein.

At the western end of Osterville's legendary Sea View Avenue--a road many believe is one of the most beautiful and valuable on all of Cape Cod reveals a property that transcends the idea of a residence. On over one acre of sweeping, tree-lined greensward with glimpses of West Bay shimmering in the distance, here is a residence that is not simply lived in, but experienced. Accessed by a winding drive of hand-laid paver stones with more than 6,342 square feet of living space, this Merle Thorpe designed home is a masterpiece of craftsmanship from a bygone era. Every lovingly maintained detail speaks to a time when artistry, skill, and pride shaped construction: mahogany windows and doors, wide-plank quarter-sawn oak floors, artisan cabinetry and moldings and graceful curved walls and rooflines that play against the endless blue of Cape Cod skies. It is at once a home and a work of art--a sculpture you inhabit, revealing new secrets and surprises with every visit. The accommodations are generous: seven bedrooms in the main house, and a generously oversized bespoke 1,000+- square foot one-bedroom guest suite with full bath, Pullman refreshment bar and laundry room above the three-car garage complete with radiant heated floors. Even the practical details carry refinement, from a dedicated trash room with an automatic air-venting system to carefully considered storage and systems. The partially finished terrace level offers a bedroom, full bath, laundry room, an additional washing room and space for your imagination to run wild. Outside, the grounds invite leisure and celebration. A 50-foot gunite pool with auto-cover is framed by a stone terrace shaded by Japanese maplesan idyllic setting for alfresco dining on summer evenings, where the sound of waves rolling onto the shore drifts from across the avenue. Ownership here includes something rare: deeded rights to a private pristine Nantucket Sound beach, just steps away, and access to Eel River, perfect for launching kayaks and paddleboards. Welcome to 850 Sea View Avenue, more than a residence; it is a legacy. Built with unmatched skill and devotion, it offers its next steward more than shelter. It is a place where cherished memories are ingrained against a backdrop of beauty and heritage and where every wall, every curve and every view reveal a story of timeless artistry. Please verify all information contained herein.

At the western end of Osterville's legendary Sea View Avenue--a road many believe is one of the most beautiful and valuable on all of Cape Cod reveals a property that transcends the idea of a residence. On over one acre of sweeping, tree-lined greensward with glimpses of West Bay shimmering in the distance, here is a residence that is not simply lived in, but experienced. Accessed by a winding drive of hand-laid paver stones with more than 6,342 square feet of living space, this Merle Thorpe designed home is a masterpiece of craftsmanship from a bygone era. Every lovingly maintained detail speaks to a time when artistry, skill, and pride shaped construction: mahogany windows and doors, wide-plank quarter-sawn oak floors, artisan cabinetry and moldings and graceful curved walls and rooflines that play against the endless blue of Cape Cod skies. It is at once a home and a work of art--a sculpture you inhabit, revealing new secrets and surprises with every visit. The accommodations are generous: seven bedrooms in the main house, and a generously oversized bespoke 1,000+- square foot one-bedroom guest suite with full bath, Pullman refreshment bar and laundry room above the three-car garage complete with radiant heated floors. Even the practical details carry refinement, from a dedicated trash room with an automatic air-venting system to carefully considered storage and systems. The partially finished terrace level offers a bedroom, full bath, laundry room, an additional washing room and space for your imagination to run wild. Outside, the grounds invite leisure and celebration. A 50-foot gunite pool with auto-cover is framed by a stone terrace shaded by Japanese maplesan idyllic setting for alfresco dining on summer evenings, where the sound of waves rolling onto the shore drifts from across the avenue. Ownership here includes something rare: deeded rights to a private pristine Nantucket Sound beach, just steps away, and access to Eel River, perfect for launching kayaks and paddleboards. Welcome to 850 Sea View Avenue, more than a residence; it is a legacy. Built with unmatched skill and devotion, it offers its next steward more than shelter. It is a place where cherished memories are ingrained against a backdrop of beauty and heritage and where every wall, every curve and every view reveal a story of timeless artistry. Please verify all information contained herein.

At the western end of Osterville's legendary Sea View Avenue--a road many believe is one of the most beautiful and valuable on all of Cape Cod reveals a property that transcends the idea of a residence. On over one acre of sweeping, tree-lined greensward with glimpses of West Bay shimmering in the distance, here is a residence that is not simply lived in, but experienced. Accessed by a winding drive of hand-laid paver stones with more than 6,342 square feet of living space, this Merle Thorpe designed home is a masterpiece of craftsmanship from a bygone era. Every lovingly maintained detail speaks to a time when artistry, skill, and pride shaped construction: mahogany windows and doors, wide-plank quarter-sawn oak floors, artisan cabinetry and moldings and graceful curved walls and rooflines that play against the endless blue of Cape Cod skies. It is at once a home and a work of art--a sculpture you inhabit, revealing new secrets and surprises with every visit. The accommodations are generous: seven bedrooms in the main house, and a generously oversized bespoke 1,000+- square foot one-bedroom guest suite with full bath, Pullman refreshment bar and laundry room above the three-car garage complete with radiant heated floors. Even the practical details carry refinement, from a dedicated trash room with an automatic air-venting system to carefully considered storage and systems. The partially finished terrace level offers a bedroom, full bath, laundry room, an additional washing room and space for your imagination to run wild. Outside, the grounds invite leisure and celebration. A 50-foot gunite pool with auto-cover is framed by a stone terrace shaded by Japanese maplesan idyllic setting for alfresco dining on summer evenings, where the sound of waves rolling onto the shore drifts from across the avenue. Ownership here includes something rare: deeded rights to a private pristine Nantucket Sound beach, just steps away, and access to Eel River, perfect for launching kayaks and paddleboards. Welcome to 850 Sea View Avenue, more than a residence; it is a legacy. Built with unmatched skill and devotion, it offers its next steward more than shelter. It is a place where cherished memories are ingrained against a backdrop of beauty and heritage and where every wall, every curve and every view reveal a story of timeless artistry. Please verify all information contained herein.

At the crossroads of coastal elegance and comfort, a rare union of high value features has emerged in a home priced under $975 PSF. Virtually unrivaled at this price point, a 5700+/- SF home consisting of twelve (12) rooms, (6) bedrooms, five (5) baths, two (2) half baths, impressively situated on 1.63+/- acres of private estate like grounds. Mature old world trees were left intact on a parcel of land with magnificent utility, absent of wetlands and adjacent to the Chatham Bike Route. There is a 400' circular driveway and lush landscaping abound securing year round privacy. The developer maintained focus on creating a home that would seamlessly merge an indoor/ outdoor living space suitable for creating unforgettable gatherings. An impressive new construction addition created a 3 car garage, 2 en suite bedrooms and a breathtaking kitchen/ living room featuring 20' ceilings, adorned with roughhewn beams, fireplace and a stately 18' wide sliders connecting the salt water pool/ patio area. An absolute gem of a property with custom fit outs throughout. All aspects of the kitchen and butler's pantry are high end cabinet shop quality, as well as all vanities and cabinets.

At the crossroads of coastal elegance and comfort, a rare union of high value features has emerged in a home priced under $975 PSF. Virtually unrivaled at this price point, a 5700+/- SF home consisting of twelve (12) rooms, (6) bedrooms, five (5) baths, two (2) half baths, impressively situated on 1.63+/- acres of private estate like grounds. Mature old world trees were left intact on a parcel of land with magnificent utility, absent of wetlands and adjacent to the Chatham Bike Route. There is a 400' circular driveway and lush landscaping abound securing year round privacy. The developer maintained focus on creating a home that would seamlessly merge an indoor/ outdoor living space suitable for creating unforgettable gatherings. An impressive new construction addition created a 3 car garage, 2 en suite bedrooms and a breathtaking kitchen/ living room featuring 20' ceilings, adorned with roughhewn beams, fireplace and a stately 18' wide sliders connecting the salt water pool/ patio area. An absolute gem of a property with custom fit outs throughout. All aspects of the kitchen and butler's pantry are high end cabinet shop quality, as well as all vanities and cabinets.

At the crossroads of coastal elegance and comfort, a rare union of high value features has emerged in a home priced under $975 PSF. Virtually unrivaled at this price point, a 5700+/- SF home consisting of twelve (12) rooms, (6) bedrooms, five (5) baths, two (2) half baths, impressively situated on 1.63+/- acres of private estate like grounds. Mature old world trees were left intact on a parcel of land with magnificent utility, absent of wetlands and adjacent to the Chatham Bike Route. There is a 400' circular driveway and lush landscaping abound securing year round privacy. The developer maintained focus on creating a home that would seamlessly merge an indoor/ outdoor living space suitable for creating unforgettable gatherings. An impressive new construction addition created a 3 car garage, 2 en suite bedrooms and a breathtaking kitchen/ living room featuring 20' ceilings, adorned with roughhewn beams, fireplace and a stately 18' wide sliders connecting the salt water pool/ patio area. An absolute gem of a property with custom fit outs throughout. All aspects of the kitchen and butler's pantry are high end cabinet shop quality, as well as all vanities and cabinets.

At the crossroads of coastal elegance and comfort, a rare union of high value features has emerged in a home priced under $975 PSF. Virtually unrivaled at this price point, a 5700+/- SF home consisting of twelve (12) rooms, (6) bedrooms, five (5) baths, two (2) half baths, impressively situated on 1.63+/- acres of private estate like grounds. Mature old world trees were left intact on a parcel of land with magnificent utility, absent of wetlands and adjacent to the Chatham Bike Route. There is a 400' circular driveway and lush landscaping abound securing year round privacy. The developer maintained focus on creating a home that would seamlessly merge an indoor/ outdoor living space suitable for creating unforgettable gatherings. An impressive new construction addition created a 3 car garage, 2 en suite bedrooms and a breathtaking kitchen/ living room featuring 20' ceilings, adorned with roughhewn beams, fireplace and a stately 18' wide sliders connecting the salt water pool/ patio area. An absolute gem of a property with custom fit outs throughout. All aspects of the kitchen and butler's pantry are high end cabinet shop quality, as well as all vanities and cabinets.

At the crossroads of coastal elegance and comfort, a rare union of high value features has emerged in a home priced under $975 PSF. Virtually unrivaled at this price point, a 5700+/- SF home consisting of twelve (12) rooms, (6) bedrooms, five (5) baths, two (2) half baths, impressively situated on 1.63+/- acres of private estate like grounds. Mature old world trees were left intact on a parcel of land with magnificent utility, absent of wetlands and adjacent to the Chatham Bike Route. There is a 400' circular driveway and lush landscaping abound securing year round privacy. The developer maintained focus on creating a home that would seamlessly merge an indoor/ outdoor living space suitable for creating unforgettable gatherings. An impressive new construction addition created a 3 car garage, 2 en suite bedrooms and a breathtaking kitchen/ living room featuring 20' ceilings, adorned with roughhewn beams, fireplace and a stately 18' wide sliders connecting the salt water pool/ patio area. An absolute gem of a property with custom fit outs throughout. All aspects of the kitchen and butler's pantry are high end cabinet shop quality, as well as all vanities and cabinets.

At the crossroads of coastal elegance and comfort, a rare union of high value features has emerged in a home priced under $975 PSF. Virtually unrivaled at this price point, a 5700+/- SF home consisting of twelve (12) rooms, (6) bedrooms, five (5) baths, two (2) half baths, impressively situated on 1.63+/- acres of private estate like grounds. Mature old world trees were left intact on a parcel of land with magnificent utility, absent of wetlands and adjacent to the Chatham Bike Route. There is a 400' circular driveway and lush landscaping abound securing year round privacy. The developer maintained focus on creating a home that would seamlessly merge an indoor/ outdoor living space suitable for creating unforgettable gatherings. An impressive new construction addition created a 3 car garage, 2 en suite bedrooms and a breathtaking kitchen/ living room featuring 20' ceilings, adorned with roughhewn beams, fireplace and a stately 18' wide sliders connecting the salt water pool/ patio area. An absolute gem of a property with custom fit outs throughout. All aspects of the kitchen and butler's pantry are high end cabinet shop quality, as well as all vanities and cabinets.

At the crossroads of coastal elegance and comfort, a rare union of high value features has emerged in a home priced under $975 PSF. Virtually unrivaled at this price point, a 5700+/- SF home consisting of twelve (12) rooms, (6) bedrooms, five (5) baths, two (2) half baths, impressively situated on 1.63+/- acres of private estate like grounds. Mature old world trees were left intact on a parcel of land with magnificent utility, absent of wetlands and adjacent to the Chatham Bike Route. There is a 400' circular driveway and lush landscaping abound securing year round privacy. The developer maintained focus on creating a home that would seamlessly merge an indoor/ outdoor living space suitable for creating unforgettable gatherings. An impressive new construction addition created a 3 car garage, 2 en suite bedrooms and a breathtaking kitchen/ living room featuring 20' ceilings, adorned with roughhewn beams, fireplace and a stately 18' wide sliders connecting the salt water pool/ patio area. An absolute gem of a property with custom fit outs throughout. All aspects of the kitchen and butler's pantry are high end cabinet shop quality, as well as all vanities and cabinets.

At the crossroads of coastal elegance and comfort, a rare union of high value features has emerged in a home priced under $975 PSF. Virtually unrivaled at this price point, a 5700+/- SF home consisting of twelve (12) rooms, (6) bedrooms, five (5) baths, two (2) half baths, impressively situated on 1.63+/- acres of private estate like grounds. Mature old world trees were left intact on a parcel of land with magnificent utility, absent of wetlands and adjacent to the Chatham Bike Route. There is a 400' circular driveway and lush landscaping abound securing year round privacy. The developer maintained focus on creating a home that would seamlessly merge an indoor/ outdoor living space suitable for creating unforgettable gatherings. An impressive new construction addition created a 3 car garage, 2 en suite bedrooms and a breathtaking kitchen/ living room featuring 20' ceilings, adorned with roughhewn beams, fireplace and a stately 18' wide sliders connecting the salt water pool/ patio area. An absolute gem of a property with custom fit outs throughout. All aspects of the kitchen and butler's pantry are high end cabinet shop quality, as well as all vanities and cabinets.

Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick fireplaces, open concept kitchen/dining room, multiple french doors, and wrap-around decks invite the outside in as sunlight & breezes waft throughout. A 1st floor primary bdrm with ample closets, ensuite bath & laundry complements the spectacular 1st floor living. Upstairs a second primary bdrm with fireplace & walk-in closet, a guest room & bath offer flexibility. The daylight lower level consists of a 4th bdrm, bath, laundry area & an unfinished room that opens to a patio with a custom masonry stone bench & fire pit. The sprawling lawn & stunning stone walls provide the perfect backdrop for a future swimming pool, tennis court & guest house or ADU. Plus potential to subdivide a 2nd lot. Minutes to the bike path, Chatham's bustling village & ocean beaches. New Roof & Boiler.

Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick fireplaces, open concept kitchen/dining room, multiple french doors, and wrap-around decks invite the outside in as sunlight & breezes waft throughout. A 1st floor primary bdrm with ample closets, ensuite bath & laundry complements the spectacular 1st floor living. Upstairs a second primary bdrm with fireplace & walk-in closet, a guest room & bath offer flexibility. The daylight lower level consists of a 4th bdrm, bath, laundry area & an unfinished room that opens to a patio with a custom masonry stone bench & fire pit. The sprawling lawn & stunning stone walls provide the perfect backdrop for a future swimming pool, tennis court & guest house or ADU. Plus potential to subdivide a 2nd lot. Minutes to the bike path, Chatham's bustling village & ocean beaches. New Roof & Boiler.

Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick fireplaces, open concept kitchen/dining room, multiple french doors, and wrap-around decks invite the outside in as sunlight & breezes waft throughout. A 1st floor primary bdrm with ample closets, ensuite bath & laundry complements the spectacular 1st floor living. Upstairs a second primary bdrm with fireplace & walk-in closet, a guest room & bath offer flexibility. The daylight lower level consists of a 4th bdrm, bath, laundry area & an unfinished room that opens to a patio with a custom masonry stone bench & fire pit. The sprawling lawn & stunning stone walls provide the perfect backdrop for a future swimming pool, tennis court & guest house or ADU. Plus potential to subdivide a 2nd lot. Minutes to the bike path, Chatham's bustling village & ocean beaches. New Roof & Boiler.

Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick fireplaces, open concept kitchen/dining room, multiple french doors, and wrap-around decks invite the outside in as sunlight & breezes waft throughout. A 1st floor primary bdrm with ample closets, ensuite bath & laundry complements the spectacular 1st floor living. Upstairs a second primary bdrm with fireplace & walk-in closet, a guest room & bath offer flexibility. The daylight lower level consists of a 4th bdrm, bath, laundry area & an unfinished room that opens to a patio with a custom masonry stone bench & fire pit. The sprawling lawn & stunning stone walls provide the perfect backdrop for a future swimming pool, tennis court & guest house or ADU. Plus potential to subdivide a 2nd lot. Minutes to the bike path, Chatham's bustling village & ocean beaches. New Roof & Boiler.

Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick fireplaces, open concept kitchen/dining room, multiple french doors, and wrap-around decks invite the outside in as sunlight & breezes waft throughout. A 1st floor primary bdrm with ample closets, ensuite bath & laundry complements the spectacular 1st floor living. Upstairs a second primary bdrm with fireplace & walk-in closet, a guest room & bath offer flexibility. The daylight lower level consists of a 4th bdrm, bath, laundry area & an unfinished room that opens to a patio with a custom masonry stone bench & fire pit. The sprawling lawn & stunning stone walls provide the perfect backdrop for a future swimming pool, tennis court & guest house or ADU. Plus potential to subdivide a 2nd lot. Minutes to the bike path, Chatham's bustling village & ocean beaches. New Roof & Boiler.

Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick fireplaces, open concept kitchen/dining room, multiple french doors, and wrap-around decks invite the outside in as sunlight & breezes waft throughout. A 1st floor primary bdrm with ample closets, ensuite bath & laundry complements the spectacular 1st floor living. Upstairs a second primary bdrm with fireplace & walk-in closet, a guest room & bath offer flexibility. The daylight lower level consists of a 4th bdrm, bath, laundry area & an unfinished room that opens to a patio with a custom masonry stone bench & fire pit. The sprawling lawn & stunning stone walls provide the perfect backdrop for a future swimming pool, tennis court & guest house or ADU. Plus potential to subdivide a 2nd lot. Minutes to the bike path, Chatham's bustling village & ocean beaches. New Roof & Boiler.

Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick fireplaces, open concept kitchen/dining room, multiple french doors, and wrap-around decks invite the outside in as sunlight & breezes waft throughout. A 1st floor primary bdrm with ample closets, ensuite bath & laundry complements the spectacular 1st floor living. Upstairs a second primary bdrm with fireplace & walk-in closet, a guest room & bath offer flexibility. The daylight lower level consists of a 4th bdrm, bath, laundry area & an unfinished room that opens to a patio with a custom masonry stone bench & fire pit. The sprawling lawn & stunning stone walls provide the perfect backdrop for a future swimming pool, tennis court & guest house or ADU. Plus potential to subdivide a 2nd lot. Minutes to the bike path, Chatham's bustling village & ocean beaches. New Roof & Boiler.

Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick fireplaces, open concept kitchen/dining room, multiple french doors, and wrap-around decks invite the outside in as sunlight & breezes waft throughout. A 1st floor primary bdrm with ample closets, ensuite bath & laundry complements the spectacular 1st floor living. Upstairs a second primary bdrm with fireplace & walk-in closet, a guest room & bath offer flexibility. The daylight lower level consists of a 4th bdrm, bath, laundry area & an unfinished room that opens to a patio with a custom masonry stone bench & fire pit. The sprawling lawn & stunning stone walls provide the perfect backdrop for a future swimming pool, tennis court & guest house or ADU. Plus potential to subdivide a 2nd lot. Minutes to the bike path, Chatham's bustling village & ocean beaches. New Roof & Boiler.

WATERFRONT ESTATE Offered for the first time in 25 years that blends classic coastal architecture with modern refinement. Built in 1994 and newly refreshed with brand-new siding and a Red Cedar roof (August 2025). Step into Cape Cod luxury with 6 bedrooms and 5 baths, a chef's kitchen, outfitted with a Viking professional gas range, Sub-Zero refrigerator, center island with prep sink, that flows seamlessly into the expansive sun-drenched living room, dining area, and waterfront sunroom. 2-car garage and full basement in the main residence for convenience and storage, plus a versatile guest house features its own 2-car garage and a captivating fieldstone fireplace. This space offers endless possibilities for multi-generational families to create a two-bedroom retreat, an artist's studio, game room, or workshop. This private estate with over 3.81 acres includes a private in-ground pool, lush landscaping, and direct access to the tidal water. This rare offering presents the chance to own not just a home, but a true Cape Cod sanctuary. A private waterfront estate designed for those who seek beauty, privacy, and an unparalleled coastal lifestyle. Some photos virtually staged