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Nestled on a beautifully elevated homesite, this classic Colonial offers the perfect blend of privacy, comfort, and New England charm. Set in a desirable neighborhood just minutes from charming Madison Village, the Town Green, shops, restaurants, and the stunning Connecticut shoreline, this home offers the perfect blend of location and lifestyle. This spacious 4-bedroom home features a welcoming living room with a fireplace, a formal dining room, an eat-in kitchen, and a generous family room with a second fireplace. A wonderful, sun porch overlooks the peaceful backyard, creating the perfect space to relax or entertain. Upstairs, you'll find four spacious bedrooms, including the primary suite with a private bath and walk-in closets. The finished lower level provides additional flexible living space for a recreation room, home office or gym. Additional highlights include a 2-car garage, newer roof, siding and windows, plus the convenience and peace of mind of natural gas and a whole-house generator. New septic tank installed to the current septic system. Neck River School district

4 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24216661 MLS

Nestled on a beautifully elevated homesite, this classic Colonial offers the perfect blend of privacy, comfort, and New England charm. Set in a desirable neighborhood just minutes from charming Madison Village, the Town Green, shops, restaurants, and the stunning Connecticut shoreline, this home offers the perfect blend of location and lifestyle. This spacious 4-bedroom home features a welcoming living room with a fireplace, a formal dining room, an eat-in kitchen, and a generous family room with a second fireplace. A wonderful, sun porch overlooks the peaceful backyard, creating the perfect space to relax or entertain. Upstairs, you'll find four spacious bedrooms, including the primary suite with a private bath and walk-in closets. The finished lower level provides additional flexible living space for a recreation room, home office or gym. Additional highlights include a 2-car garage, newer roof, siding and windows, plus the convenience and peace of mind of natural gas and a whole-house generator. New septic tank installed to the current septic system. Neck River School district

7 Milestone Ln, Madison

$599,000

Timeless New England charm meets contemporary style in this beautifully remodeled Cape, where classic character and thoughtful modern updates come together effortlessly. The inviting interior features an open-concept kitchen and dining area designed for both everyday living and effortless entertaining. Just off the kitchen, a lovely deck extends the living space outdoors, creating the perfect setting for al fresco dining, relaxed afternoons, and gathering with family and friends. The spacious living room, centered around a wood-burning fireplace, offers warmth and timeless appeal. Two generously sized bedrooms, beautifully updated bathrooms, and California Closets provide comfort and refined functionality. The completely reimagined basement offers exceptional versatility, with flexible bonus spaces ideal for a home office, guest retreat, gym, playroom, or additional living area. A garage adds convenience and valuable storage. Ideally situated near town, local shops, beautiful beaches, and a brand-new elementary school, this home offers the best of coastal New England living, blending enduring charm, modern comfort, and a location that makes everyday life feel just a little more special.

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24215402 MLS

Timeless New England charm meets contemporary style in this beautifully remodeled Cape, where classic character and thoughtful modern updates come together effortlessly. The inviting interior features an open-concept kitchen and dining area designed for both everyday living and effortless entertaining. Just off the kitchen, a lovely deck extends the living space outdoors, creating the perfect setting for al fresco dining, relaxed afternoons, and gathering with family and friends. The spacious living room, centered around a wood-burning fireplace, offers warmth and timeless appeal. Two generously sized bedrooms, beautifully updated bathrooms, and California Closets provide comfort and refined functionality. The completely reimagined basement offers exceptional versatility, with flexible bonus spaces ideal for a home office, guest retreat, gym, playroom, or additional living area. A garage adds convenience and valuable storage. Ideally situated near town, local shops, beautiful beaches, and a brand-new elementary school, this home offers the best of coastal New England living, blending enduring charm, modern comfort, and a location that makes everyday life feel just a little more special.

182 Green Hill Rd, Madison

$599,000

Welcome to this beautifully maintained home on a cul-de-sac street. Low traffic, great for play. When entering this inviting home, the foyer greets you with the natural light of the main living room's oversized windows creating a bright ambience that flows seamlessly into the eat-in kitchen and dining area. The updated kitchen features newer stainless steel appliances (2024), while beautiful hardwood floors add warmth and character throughout the main level. Just a few steps up, you'll find three generously sized bedrooms,including a spacious primary bedroom, all featuring beautiful hardwood floors that continue into the hallway. Entire interior painted, along with new interior doors (2024). The versatile lower level offers additional living space, complete with a cozy raised hearth fireplace w/newer wood-burning/pellet stove (2023), newly renovated full bathroom and laundry area(2020). Whether you envision a comfortable family room, home office,or creative retreat,this space offers endless possibilities. Step outside onto the expansive deck overlooking a lush,lovingly landscaped property and spacious, level yard.This private outdoor oasis is perfect for summer entertaining,relaxing evenings, or simply enjoying the peaceful surroundings. Complete with a two-car garage and ideally situated just minutes from schools (Neck River, Polson,Hand) the shoreline, shopping, restaurants, and interstates, this home offers the perfect combination of style, functionality, and convenience.

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24214239 MLS

Welcome to this beautifully maintained home on a cul-de-sac street. Low traffic, great for play. When entering this inviting home, the foyer greets you with the natural light of the main living room's oversized windows creating a bright ambience that flows seamlessly into the eat-in kitchen and dining area. The updated kitchen features newer stainless steel appliances (2024), while beautiful hardwood floors add warmth and character throughout the main level. Just a few steps up, you'll find three generously sized bedrooms,including a spacious primary bedroom, all featuring beautiful hardwood floors that continue into the hallway. Entire interior painted, along with new interior doors (2024). The versatile lower level offers additional living space, complete with a cozy raised hearth fireplace w/newer wood-burning/pellet stove (2023), newly renovated full bathroom and laundry area(2020). Whether you envision a comfortable family room, home office,or creative retreat,this space offers endless possibilities. Step outside onto the expansive deck overlooking a lush,lovingly landscaped property and spacious, level yard.This private outdoor oasis is perfect for summer entertaining,relaxing evenings, or simply enjoying the peaceful surroundings. Complete with a two-car garage and ideally situated just minutes from schools (Neck River, Polson,Hand) the shoreline, shopping, restaurants, and interstates, this home offers the perfect combination of style, functionality, and convenience.

16 Tamarac Dr, Madison

$6,000

TIMELESS 1910 CHARM MEETS MODERN COMFORT IN DOWNTOWN MADISON! Step into a perfect blend of historic character and contemporary convenience with this beautifully renovated 1910 home in an unbeatable downtown Madison location. From the moment you arrive, the oversized front porch welcomes you to sit back and enjoy the vibrant neighborhood atmosphere. Inside, stunning original hardwood floors and classic vintage features flow throughout a spacious, light-filled floor plan. The expansive living room offers abundant space for gathering, while the updated kitchen provides the modern functionality you need for everyday living and entertaining. Unwind in the cozy sunroom-a serene spot for reading or taking in natural light year-round. Featuring 4 generous bedrooms on the 2nd floor, this home easily adapts to your lifestyle, whether you need dedicated work-from-home spaces or extra guest rooms. Offered partially furnished and situated just moments from local shops, dining, and town amenities, this property delivers the ultimate in-town lifestyle.

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24211360 MLS

TIMELESS 1910 CHARM MEETS MODERN COMFORT IN DOWNTOWN MADISON! Step into a perfect blend of historic character and contemporary convenience with this beautifully renovated 1910 home in an unbeatable downtown Madison location. From the moment you arrive, the oversized front porch welcomes you to sit back and enjoy the vibrant neighborhood atmosphere. Inside, stunning original hardwood floors and classic vintage features flow throughout a spacious, light-filled floor plan. The expansive living room offers abundant space for gathering, while the updated kitchen provides the modern functionality you need for everyday living and entertaining. Unwind in the cozy sunroom-a serene spot for reading or taking in natural light year-round. Featuring 4 generous bedrooms on the 2nd floor, this home easily adapts to your lifestyle, whether you need dedicated work-from-home spaces or extra guest rooms. Offered partially furnished and situated just moments from local shops, dining, and town amenities, this property delivers the ultimate in-town lifestyle.

25 Wall St, Madison

$399,000

Tucked away on a private setting high above Scotland Road, 270 Scotland Road offers the perfect combination of privacy, space, and natural beauty. Set on approximately 2 acres of lightly wooded land, this 3-bedroom, 1.5-bath raised ranch enjoys elevated surroundings with seasonal views toward the Hammonasset River. The main level features a comfortable, flowing layout with hardwood floors throughout the spacious living room, complete with a fireplace that creates a warm and inviting focal point. The updated kitchen offers stainless steel appliances, tiled flooring, and a generous dining area with plenty of space for everyday living and entertaining. Three bedrooms and a full and half bath are conveniently located on the main level. Downstairs, you'll find additional finished living space with a beautiful brick fireplace, offering flexibility for a family room, home office, recreation area, or guest space. Set back in a private, lightly wooded setting, this home offers the opportunity to enjoy the peace and privacy of acreage while remaining conveniently located in Madison. With its elevated setting, river views, spacious lot, and flexible living space, 270 Scotland Road is a property worth seeing in person.

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24210705 MLS

Tucked away on a private setting high above Scotland Road, 270 Scotland Road offers the perfect combination of privacy, space, and natural beauty. Set on approximately 2 acres of lightly wooded land, this 3-bedroom, 1.5-bath raised ranch enjoys elevated surroundings with seasonal views toward the Hammonasset River. The main level features a comfortable, flowing layout with hardwood floors throughout the spacious living room, complete with a fireplace that creates a warm and inviting focal point. The updated kitchen offers stainless steel appliances, tiled flooring, and a generous dining area with plenty of space for everyday living and entertaining. Three bedrooms and a full and half bath are conveniently located on the main level. Downstairs, you'll find additional finished living space with a beautiful brick fireplace, offering flexibility for a family room, home office, recreation area, or guest space. Set back in a private, lightly wooded setting, this home offers the opportunity to enjoy the peace and privacy of acreage while remaining conveniently located in Madison. With its elevated setting, river views, spacious lot, and flexible living space, 270 Scotland Road is a property worth seeing in person.

270 Scotland Rd, Madison

$600,000

**Offered for the first time in over 54 years, this oversized ranch provides exceptional space, flexibility, and charm. Originally built in 1972 by a longtime Madison resident for his two daughters, this 2,240squarefoot home has been thoughtfully designed to accommodate a variety of living arrangements. Located in Madison's desirable southern section on a generous 1.33acre lot, the property offers convenient access to the downtown village, sandy town beaches, Hammonasset State Park's walking trails, and Madison's Town Campus. It's a rare opportunity to enjoy privacy while remaining close to everything Madison has to offer. This unique residence was constructed as a true duplex ranch, featuring two full kitchens, two living rooms, and two full baths-all connected and all on one level. A welcoming front foyer provides two separate entrances, complemented by two additional rear entrances. With three bedrooms on one side and two bedrooms on the other, the layout is ideal for an inlaw suite, multigenerational living, or simply enjoying the benefit of five total bedrooms and abundant square footage. Craftsmanship from a bygone era is evident throughout, with many rooms showcasing the original parquet hardwood floors. Both kitchens open directly to the expansive and private rear yard, offering wonderful outdoor enjoyment and potential for future expansion if desired. Don't miss this rare chance to own two homes in one-a truly special offering in Madison.

5 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24210111 MLS

**Offered for the first time in over 54 years, this oversized ranch provides exceptional space, flexibility, and charm. Originally built in 1972 by a longtime Madison resident for his two daughters, this 2,240squarefoot home has been thoughtfully designed to accommodate a variety of living arrangements. Located in Madison's desirable southern section on a generous 1.33acre lot, the property offers convenient access to the downtown village, sandy town beaches, Hammonasset State Park's walking trails, and Madison's Town Campus. It's a rare opportunity to enjoy privacy while remaining close to everything Madison has to offer. This unique residence was constructed as a true duplex ranch, featuring two full kitchens, two living rooms, and two full baths-all connected and all on one level. A welcoming front foyer provides two separate entrances, complemented by two additional rear entrances. With three bedrooms on one side and two bedrooms on the other, the layout is ideal for an inlaw suite, multigenerational living, or simply enjoying the benefit of five total bedrooms and abundant square footage. Craftsmanship from a bygone era is evident throughout, with many rooms showcasing the original parquet hardwood floors. Both kitchens open directly to the expansive and private rear yard, offering wonderful outdoor enjoyment and potential for future expansion if desired. Don't miss this rare chance to own two homes in one-a truly special offering in Madison.

273 Horse Pond Rd, Madison

$2,800

This home is available from October 1 through May of 2027 as a furnished academic rental. Enjoy the comfort of this 2-3 bedroom home with a wonderful beach at the end of the street. From the living room through the updated kitchen is beautiful new flooring. A cute separate dining room is off of the kitchen. At the back of the house is a cozy den and a porch enclosed with sliding glass doors. A bedroom with a full updated bath nearby is on the 1st floor. Upstairs is a full 2nd bedroom and a full bath with an option for a 3rd bedroom or office space.

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24204883 MLS

This home is available from October 1 through May of 2027 as a furnished academic rental. Enjoy the comfort of this 2-3 bedroom home with a wonderful beach at the end of the street. From the living room through the updated kitchen is beautiful new flooring. A cute separate dining room is off of the kitchen. At the back of the house is a cozy den and a porch enclosed with sliding glass doors. A bedroom with a full updated bath nearby is on the 1st floor. Upstairs is a full 2nd bedroom and a full bath with an option for a 3rd bedroom or office space.

41 Harbor Ave, Madison

$650,000

BEACH HOME! BEACH RIGHTS! NEEDS WORK! It is not everyday that an opportunity to own a double lot in such a shoreline area. This charming English Cottage-style Cape, situated on a generous footprint for the area, is ready for it's next chapter-whether that involves a thoughtful renovation or the construction of a brand-new coastal home perhaps. Residents enjoy deeded rights to a private association sandy beach located just at the end of the street! The main residence of which there are no photos for obvious reasons once you see it (NEEDS WORK) currently features three bedrooms and 1.5 baths but adding to the property's versatility is a delightful in good condition accessory apartment, which offers a full kitchen, full bath, a private bedroom and a cozy living area anchored by a stone fireplace and two separate exterior entrances. This setup is ideal for multi-generational living, a great guest suite or potential rental income. Maybe live in this while redoing the other portion. The property is a double lot that accommodates four dedicated parking spaces - a true luxury for beachside living. Best of all, the property is located where no flood insurance is required, offering peace of mind alongside the salt air. Whether you choose to polish this unique gem or start fresh with a custom build, this is the perfect canvas for your seaside lifestyle.

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24172475 MLS

BEACH HOME! BEACH RIGHTS! NEEDS WORK! It is not everyday that an opportunity to own a double lot in such a shoreline area. This charming English Cottage-style Cape, situated on a generous footprint for the area, is ready for it's next chapter-whether that involves a thoughtful renovation or the construction of a brand-new coastal home perhaps. Residents enjoy deeded rights to a private association sandy beach located just at the end of the street! The main residence of which there are no photos for obvious reasons once you see it (NEEDS WORK) currently features three bedrooms and 1.5 baths but adding to the property's versatility is a delightful in good condition accessory apartment, which offers a full kitchen, full bath, a private bedroom and a cozy living area anchored by a stone fireplace and two separate exterior entrances. This setup is ideal for multi-generational living, a great guest suite or potential rental income. Maybe live in this while redoing the other portion. The property is a double lot that accommodates four dedicated parking spaces - a true luxury for beachside living. Best of all, the property is located where no flood insurance is required, offering peace of mind alongside the salt air. Whether you choose to polish this unique gem or start fresh with a custom build, this is the perfect canvas for your seaside lifestyle.

67 Blakeman Rd, Madison

$900,000

Build Your Dream Home on Prestigious Lantern Hill Road Discover an exceptional opportunity to own a 1.2acre parcel tucked away on one of Madison's most coveted and private culdesacs. Located at 78 Lantern Hill Road, this hidden gem offers the perfect balance of tranquility and convenience-less than a mile from Madison's beautiful beaches, vibrant town center, boutique shopping, dining, golf, and quick access to I95 for effortless commuting. Surrounded by impeccably maintained, luxury homes-many valued around the $3 million mark-this premier lot provides an ideal canvas for an elegant coastal residence. Mature trees, serene natural surroundings, and underground utilities enhance the setting, making it ready for a highend build that complements the neighborhood's sophistication. Experience the best of shoreline living in Madison, celebrated for its charming village atmosphere, thriving arts and culture, abundant recreation, and pristine coastline. Whether you envision a yearround sanctuary or a summer retreat, this location offers a rare blend of privacy, luxury, and accessibility. Don't miss the chance to build in one of Connecticut's most soughtafter seaside communities.

ACTIVE Status ⋅ 24200319 MLS

Build Your Dream Home on Prestigious Lantern Hill Road Discover an exceptional opportunity to own a 1.2acre parcel tucked away on one of Madison's most coveted and private culdesacs. Located at 78 Lantern Hill Road, this hidden gem offers the perfect balance of tranquility and convenience-less than a mile from Madison's beautiful beaches, vibrant town center, boutique shopping, dining, golf, and quick access to I95 for effortless commuting. Surrounded by impeccably maintained, luxury homes-many valued around the $3 million mark-this premier lot provides an ideal canvas for an elegant coastal residence. Mature trees, serene natural surroundings, and underground utilities enhance the setting, making it ready for a highend build that complements the neighborhood's sophistication. Experience the best of shoreline living in Madison, celebrated for its charming village atmosphere, thriving arts and culture, abundant recreation, and pristine coastline. Whether you envision a yearround sanctuary or a summer retreat, this location offers a rare blend of privacy, luxury, and accessibility. Don't miss the chance to build in one of Connecticut's most soughtafter seaside communities.

78 Lantern Hill Rd, Madison

$7,500

Relocating to the area? House hunting and yet to find the perfect home? Perhaps looking to spend the academic year along the gorgeous CT shoreline? Look no further as you've found the perfect spot to hang your hat for the academic year here at 32 Tuxis Road. This home is a beautifully restored, quintessential Madison beach house available for rent from September 8, 2026 - June 30, 2027. Originally built in 1915, and maintaining much of the original architecture, this renovated home offers a blend of old world charm and modern luxuries. Desirable open floor plan, chef's kitchen, 5 well sized bedrooms, 4.5 bathrooms and walkable to 3 beaches this house offers all you could desire from a rental. Immaculate condition and desirable location! Dogs considered. Landlord to cover cable, wifi, landscaping, snow plowing and trash removal. Tenant to cover electricity, water, propane and all other utilities. No garage bays and large primary walk-in closet available. Two month's security required.

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24194730 MLS

Relocating to the area? House hunting and yet to find the perfect home? Perhaps looking to spend the academic year along the gorgeous CT shoreline? Look no further as you've found the perfect spot to hang your hat for the academic year here at 32 Tuxis Road. This home is a beautifully restored, quintessential Madison beach house available for rent from September 8, 2026 - June 30, 2027. Originally built in 1915, and maintaining much of the original architecture, this renovated home offers a blend of old world charm and modern luxuries. Desirable open floor plan, chef's kitchen, 5 well sized bedrooms, 4.5 bathrooms and walkable to 3 beaches this house offers all you could desire from a rental. Immaculate condition and desirable location! Dogs considered. Landlord to cover cable, wifi, landscaping, snow plowing and trash removal. Tenant to cover electricity, water, propane and all other utilities. No garage bays and large primary walk-in closet available. Two month's security required.

32 Tuxis Rd, Madison

$3,000,000

Exceptionally located less than a tenth of a mile from both the town green and beaches - with your own private beach access - this stunning residence sits on 1.57 secluded acres and has been completely re-imagined with uncompromising attention to detail and the finest materials. The home offers 16 thoughtfully designed rooms. Sun filled interiors feature over sized windows and expansive sight lines, anchored by a massive family room and a top of the line chef's kitchen. The lower level is a true walkout guest suite with additional living space plus a separate garage apartment for overnight guests. Outside amenities evoke a private resort: a gunite pool, extensive stone patios, two fully equipped outdoor kitchens, and a charming grassy area framed by mature landscaping for complete privacy. This is a rare coastal estate that blends modern, high end finishes with relaxed, year round seaside living. Practical luxury continues with a three car garage, circular driveway, and generous storage. This is truly a must see, and all reasonable offers will be entertained.

5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24166497 MLS

Exceptionally located less than a tenth of a mile from both the town green and beaches - with your own private beach access - this stunning residence sits on 1.57 secluded acres and has been completely re-imagined with uncompromising attention to detail and the finest materials. The home offers 16 thoughtfully designed rooms. Sun filled interiors feature over sized windows and expansive sight lines, anchored by a massive family room and a top of the line chef's kitchen. The lower level is a true walkout guest suite with additional living space plus a separate garage apartment for overnight guests. Outside amenities evoke a private resort: a gunite pool, extensive stone patios, two fully equipped outdoor kitchens, and a charming grassy area framed by mature landscaping for complete privacy. This is a rare coastal estate that blends modern, high end finishes with relaxed, year round seaside living. Practical luxury continues with a three car garage, circular driveway, and generous storage. This is truly a must see, and all reasonable offers will be entertained.

45 Island Ave, Madison

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