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17 Homes For Sale in The Neighborhood Of Old Hill In Westport, CT

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$1,550,000Est. Payment
4 Beds | 5 Baths | 5,617 Sqft

29 Grassy Plains Road #29, Westport, CT 06880

Condominium For Sale

The perfect combination of home and surroundings you've been looking for! The Reserve at Poplar Plains is a PUD community of 13 free standing homes surrounded by 33 acres of woodland, babbling brooks and ponds - all the benefits of the privacy of a single family home without the aggravation of being responsible for outdoor maintenance. This is a pristine, custom home, with multiple upgrades such as a full house generator, Viking and Wolf appliances, even a blue tooth controlled steam shower and heated floors in the master bathroom! Of course there's a mud room, and of course there's a walk in pantry. And yes, the first floor ceilings are 9 feet high. The four bedrooms all have custom designed cabinetry in the walk in closets and ensuite baths. The private office overlooks the natural beauty of the woodlands. The newly finished lower level with 9 foot ceilings adds another 1449 finished square feet of living space, bringing the total finished space in the home to 5617 square feet on three levels. Conveniently located at the intersections of Westport, Wilton, and Norwalk, living at Poplar Plains allows you access to multiple choices for shopping and fine dining in about five minutes. Only one mile to the Merritt Parkway, and a straight shot to downtown Westport, I-95 and your choice of train stations. This is just easy.

$1,550,000Est. Payment
4 Beds | 5 Baths | 5,617 Sqft

29 Grassy Plains Road, Westport, CT 06880

House For Sale

The perfect combination of home and surroundings you've been looking for! The Reserve at Poplar Plains is a PUD community of 13 free standing homes surrounded by 33 acres of woodland, babbling brooks and ponds - all the benefits of the privacy of a single family home without the aggravation of being responsible for outdoor maintenance. This is a pristine, custom home, with multiple upgrades such as a full house generator, Viking and Wolf appliances, even a blue tooth controlled steam shower and heated floors in the master bathroom! Of course there's a mud room, and of course there's a walk in pantry. And yes, the first floor ceilings are 9 feet high. The four bedrooms all have custom designed cabinetry in the walk in closets and ensuite baths. The private office overlooks the natural beauty of the woodlands. The newly finished lower level with 9 foot ceilings adds another 1449 finished square feet of living space, bringing the total finished space in the home to 5617 square feet on three levels. Conveniently located at the intersections of Westport, Wilton, and Norwalk, living at Poplar Plains allows you access to multiple choices for shopping and fine dining in about five minutes. Only one mile to the Merritt Parkway, and a straight shot to downtown Westport, I-95 and your choice of train stations. This is just easy.

$3,099,000Est. Payment
7 Beds | 9 Baths | 10,272 Sqft

7 Old Hill Farms Road, Westport, CT 06880

House For Sale

Grand scale, comfortable proportions & a thoughtful layout define this timeless Colonial set on a landscaped, level, acre on one of Westport's premier Old Hill streets. Finished on four floors, with 7 bedrooms & 7 full/2 half baths, this home was designed for easy living with all the extra spaces and luxurious details one would expect at this level. A soaring entry foyer, custom wood-paneled office, open eat-in kitchen w top of the line appliances, 2 Dishwashers & walk in pantry, oversized family room, expansive dining room, light filled living room & cheerful sunroom complete the first floor. Upstairs is a sumptuous Master Bedroom Suite with fireplace & separate sitting room, custom walk in closets (incl a dedicated W/D), decadent bath w steam shower & a soaking tub Down the hall are four additional bedrooms, all en-suite, a large recreation room & laundry room. The third floor offers a 6th bedroom with full bath & add'l living space - currently outfitted as a gym - with a Peloton bike that comes with the house! The fully finished walk-out lower level is a destination unto itself with a 7th bedroom, full bath & multiple recreation spaces for work & play. Outside, an oversized bluestone patio overlooks the lushly landscaped full acre property with heated Gunite pool/spa w safety cover & fence. Heated 3 car garage & full house generator. Privately situated on a celebrated Westport street, in close walking distance to shopping & cafes and minutes to train & beach.

$1,490,000Est. Payment
5 Beds | 4 Baths | 4,473 Sqft

4 River Lane, Westport, CT 06880

House For Sale

Opportunity Knocks! Enjoy serene river front living from this spacious 4400+ square foot 5 bedroom, 3.5 bath Colonial. Relax poolside in this peaceful country setting with captivating views and access to the Saugatuck River. Kayak or paddle board in your own backyard! The open floorplan offers double living room with 2 fireplaces. The cooks kitchen, features large center island with breakfast bar, custom cabinetry, quartz counter tops, opens onto the great room with office. Fifth bedroom with full bath is on main level. Second level includes 4 oversized bedrooms, hardwood floors and 2 full baths. The finished, walkout lower level, opens onto screened porch with stone floor overlooking, bucolic grounds, heated gunite pool and spa. Plus generator. Minutes to downtown, schools and train.

$1,795,000Est. Payment
4 Beds | 3 Baths | 3,465 Sqft

8 River Lane, Westport, CT 06880

House For Sale

Resting high above the glistening Saugatuck River, mins to the center of town, is this effortlessly chic 1929 Cape that blends iconic character + elegance with practical luxury. Characterized by well-proportioned rooms, a comfortable flow + an eclectic flair, the interior spaces are bathed in light by the many windows and french doors. Situated on the River side of this beloved street, an oversized terrace flanks the entire rear of the home offering soaring views above the trees to the glorious water, below. The central living spaces are comfortable, not overdone, designed to embrace the original period details w a clean, updated, aesthetic. The Cooks kitchen w large center island features custom cabinetry + Carrera marble countertops. A casual dining area connects the kitchen to the family room, w soaring beamed ceilings, FP + terrace access. The formal dining room provides the ideal backdrop for family gatherings around the table. The living rm is a perfect spot to connect, or disconnect, by the fire. An adjacent home office/playroom completes the 1st floor. Upstairs are 4 spacious beds incl a luxurious MBS complete with walk-in closets, sitting rm + bath w steam shower and jetted tub. 2 add'l beds share a renovated bath. The 3rd bedroom is impeccably designed with custom seating and a stunning en-suite bath. Set on 1.26 acres with level yard area, lovely gardens and rm for a pool. 2 car garage. Outdoor pizza oven set amongst the trees is a destination unto itself.

$60,274
$1,099,626Est. Payment
4 Beds | 4 Baths | 4,559 Sqft

4 Bolton Lane, Westport, CT 06880

House For Sale

Welcome to the most wonderful block in Westport. Create the lifestyle you dream about, in this premier cul-de-sac neighborhood of exquisite homes. Just a five minute drive to the shops on Main Street, this expanded New England cape has room for everyone and more! Featuring a brand new roof, with property that abuts the river front, you can relax at home in your own backyard oasis, surrounded by nature. Conveniently located to Metro North and both major highways, this spacious home has a bright and airy classic floor plan, with large bay windows and tons of natural light. The formal dining room is a focal point of the house where memories are made as you entertain for parties of 10 and more. 3 nicely scaled bedrooms, large kitchen, den, 2 full baths and sunroom fill out the main house with tons of storage and a walk-in closet that can be dormered to add another bedroom. There are multiple large spaces on the second floor that can easily be incorporated into bedroom square footage. There is a huge first floor legal in law space that's comprised of a great-room, vaulted ceilings, dining area, kitchen, bedroom with a full bath ensuite. The in-law has a separate entrance and can be incorporated to the main house as a family room and entertainment center. The walk out lower level offers plenty of room for fun, storage, a separate laundry room and half bath. Adjacent to the rec room is space for a home office or storage space along with access to a two car garage. SEE VIRTUAL TOUR

$699,000Est. Payment
3 Beds | 4 Baths | 2,054 Sqft

269 Wilton Road, Westport, CT 06880

House For Sale

OPPORTUNITY KNOCKS! First time on market in over 30 years. Beautiful light filled Colonial situated on one flat acre. Formal Living Room, Formal Dining Room, Eat-In-Kitchen plus Office and Sun-filled Porch on first floor. Second floor includes Master Bedroom with bath and 2 additional Bedrooms. Full basement with 864 sqft. finished basement with half bath. Renovate or rebuild to make this your dream home! This is a MUST SEE!!

$1,749,000Est. Payment
4 Beds | 5 Baths | 5,480 Sqft

17 April Drive, Westport, CT 06880

House For Sale

2020 Custom Restored Post & Beam Timber Constructed home with huge windows, authentic silo with custom staircase & gated & expansive yard. Soaring ceilings, light-filled rooms, custom design features & beautiful exposed woodwork create a place unlike any other currently on the market. Finished on 3 levels this house offers high-end quality from top to bottom & an efficient balance of living space to accommodate today's growing family & friends. Wonderful great room with wood-burning fireplace & office/study are sun-drenched by a floor to ceiling wall of windows. The family room & dining area are perfectly tucked off the gourmet eat-in kitchen with custom cabinetry & sliders to a fantastic deck overlooking a wonderful outdoor firepit, patio & private backyard. A comfortable master suite & bathroom with separate spa room complete the first floor. On the 2nd floor, 2 additional ensuite bedrooms each with separate sitting lofts connect to all 3 floors via a custom wood & metal spiral staircase cleverly built into the silo. The expansive walkout lower level features a large play/media room w/wine cellar, gym, wet bar, a flex room or potential bedroom w/large closet, & full bathroom. Oversized 2 car garage with large finished space w/private entrance offers a 4th bedroom option. Tucked quietly away at the end of a cul-de-sac conveniently located close to the center of Westport & perfect proximity to the Merrit and train this home is solidly built from top to bottom.Room for a pool.

$1,699,000Est. Payment
4 Beds | 4 Baths | 3,543 Sqft

14 River Lane, Westport, CT 06880

House For Sale

Rare opportunity to live perched above the beautiful Saugatuck River. Nothing like it in Westport. This special stone and wood shingle home has captivating views and sounds of the waterfall and the river far below. Sit outdoors at the salt water pool or new hot tub and benefit from this unique and close to town location or relax inside in either the welcoming great room with fireplace, or the screened porch or the kitchen family room combination with its exposed beam ceiling and its own cozy fireplace. Hard to describe the feel of this warm home. Four large ensuite bedrooms, updated baths and a feeling of serenity. You will not want to leave! Square footage is three levels totally 3543 square feet. (2743 on main and bedroom levels and 800 on walk out ground floor level.)

$2,299,000Est. Payment
5 Beds | 5 Baths | 5,251 Sqft

15 Partrick Lane, Westport, CT 06880

House For Sale

Stunning French country sophistication tucked away on a cul-de-sac in the Old Hill Section of Westport.What a treat for the entertaining family! The main floor has an open floor plan with wooden beams,fireplace, hwd floors,and magnificent windows with 360 degrees of the outdoors.Custom chef's kitchen with wood burning pizza oven, expresso coffee machine, Miele SS appliances ,wine cellar with a glass floor to enjoy your collection.There's an outdoor kitchen with a separate rotisserie pit for all your BBQ needs. The main bedroom ensuite with a soaking tub, shower and his and her sinks, three addl ensuites plus 2Brs w/shared bath. There is a secondary living area with all natural light, high ceilings,3 car garage and more.Truely one of a kind home. Room for 40' pool.Near walking trails.

$70,000
$799,000Est. Payment
4 Beds | 2 Baths | 2,950 Sqft

251 Wilton Road, Westport, CT 06880

House For Sale

BEST VALUE UNDER 900K IN WESTPORT! Instant equity in this vintage cape that is priced well below appraised value. It is privately set back from the road on over an acre and a half of land nestled among beautiful mature trees. The open flow of the main level gives sight lines from the living room to the dining room to the kitchen to the family room. Hardwood floors throughout. Great for entertaining or watching children from any room. The chef's kitchen is designed with a great working island that also has seating, a stunning brick fireplace in the eating nook and a huge walk in pantry. Off the family room is an expansive deck with views out over the rolling property that is large enough to incorporate a pool. Four well proportioned bedrooms, one being used as an office and 2 full baths complete the home. The massive basement has a playroom, storage area, laundry and a 2 car garage. Brand new windows just installed throughout and the bonus of a whole house generator to complete the package. Unpack your bags and move right in! LOOKING FOR SOMETHING TO RENOVATE AND FLIP? CHECK OUT THE SECOND FLOOR RENOVATION PLAN FOR AN EASY MASTER SUITE ADDITION.

$5,874,000Est. Payment
6 Beds | 9 Baths | 13,161 Sqft

2 Broadview Road, Westport, CT 06880

House For Sale

MOTIVATED SELLERS will entertain all reasonable offers. 60-mins from NYC! Set amid acres of matured specimen plantings, this New England shingle style home is a classically inspired masterpiece. With 6 bedrooms & 9 bathrooms as well as a paneled library, staff quarters, movie screening & recreation rooms, the home displays a blend of classic design & the finest craftsmanship. Fine materials & finishes distinguish the home, further refined by vaulted ceilings & details including, superior woodwork, walls of windows & French doors that drench the home in natural light & present vistas of the surrounding grounds. Modern amenities, such as state-of-the-art kitchen, expansive entertaining spaces, balance the homes classical influences with the highest technology in its most functional form.

$175,000
$1,125,000Est. Payment
3.1 Acres

46 Partrick Road, Westport, CT 06880

Lots Land For Sale

Pool, tennis court, sport court, guest house...you can have it all! Build the home of your dreams on 3.1 buildable acres in Westport's coveted Old Hill neighborhood. Minutes to Merritt Parkway, Main Street and all that this magical New England town has to offer. Vacant land with no structures on property. No wetlands.

$2,500,000Est. Payment
5 Beds | 7 Baths | 7,250 Sqft

5 Winding Court, Westport, CT 06880

House For Sale

NEW CONSTRUCTION - TO BE BUILT ON A COVETED OLD HILL PRIVATE ROAD/PREMIER NEIGHBORHOOD - Renowned, luxury builder Mattera Construction is well-known for architecturally significant & stunning homes filled with elegance, timeless beauty, luxurious interiors with state of the art amenities. Now offering a perfectly designed home filled with light & elegant finishes. Featuring an expansive foyer, grand staircase, 10 ft ceilings on the first floor, open, living spaces throughout. Breathtaking kitchen, family room, master suite and more, this builder is unparalleled in his work. Well sited on a private level acre with pool site. Minutes to the train, beach, & town. Unique opportunity to customize this exceptional residence by the most sought after craftsman who consistently builds each masterpiece with ingenuity and integrity. (Photos represent a sample of Mattera's recent work.)

$225,000
$1,750,000Est. Payment
6 Beds | 8 Baths | 9,110 Sqft

Westport, CT 06880

House For Sale

Exquisite Old Hill colonial with over 7500 sq. ft. situated on 2.99 wooded acres. Enjoy the privacy of the rear deck overlooking the stone patio, heated pool and spa. This custom built home features a grand two story entry with radiant heated marble floors. Formal living room with fireplace, formal dining room, an office, a library and a large family room with fireplace are all on the main level. The gourmet kitchen includes an island with granite counters, Wolf and Sub Zero appliances including 2 dishwashers and a wine cooler. Entering the upper level master suite you will discover a fireplace, marble/onyx master bath, a study, 2 walk in cherry closets and a dressing room. There are 4 additional en suite bedrooms and a study on this level. The fully finished lower level, which provides access to the pool and spa, also offers a playroom, exercise room, media/pool room and a separate au pair suite with full bath. This home provides private gracious living while being close to town, trains and highways.

$799,999Est. Payment
3 Beds | 2 Baths | 1,853 Sqft

48 Woodside Avenue, Westport, CT 06880

House For Sale

Charming Westport farmhouse! With 3 bedrooms and 2 full baths, 48 Woodside Ave is set on a half acre of pretty Old Hill property. Just a stone's throw from Nash Pond, an easy walk to downtown Westport or the natural preserves of Earthplace and Lillian Wadsworth Arboretum, its a convenient location in a country setting. Built in 1920, the opportunity to own a home with history and character awaits!

$--Est. Payment
-- Beds | -- Baths | -- Sqft

Westport, CT 06880

House For Sale

This property is in initial default, also known as Pre-Foreclosure. The homeowner of this property has missed at least one payment and is now considered delinquent. In order to avoid a full foreclosure, the homeowner may be willing to sell this home at an attractive price. No asking price is posted on Pre Foreclosures because these properties are not formally listed on the market for sale, yet. Instead, the original loan balance is presented. Use this amount, along with local sale price comparables to establish a reasonable offer on this home.

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